Pyrrolidine → 6-cyano-3,4-dihydro-2,2-bis(methoxymethyl)-2H-1-benzopyran-4-one

HRID 862478Notes

Reaction equation

HRID 862478 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[OH:12])=[O:3].N1CCCC1.[CH3:18][O:19][CH2:20][C:21](=O)[CH2:22][O:23][CH3:24]>C1(C)C=CC=CC=1>[C:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:12][C:21]([CH2:22][O:23][CH3:24])([CH2:20][O:19][CH3:18])[CH2:1][C:2](=[O:3])[C:4]=2[CH:9]=1)#[N:11]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 15018881,3-DimethoxyacetoneHCID 123328323-Acetyl-4-hydroxybenzonitrile

Product 1

HCID 107301156-cyano-3,4-dihydro-2,2-bis(methoxymethyl)-2H-1-benzopyran-4-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Cyano-2-hydroxyacetophenone (13.57 g) was dissolved in toluene (120 ml), and pyrrolidine (6 ml) and 1,3-dimethoxy-2-propanone (15 ml) were added. The mixture was refluxed under heating for 1 hour while removing the generated water. After cooling, the reaction mixture was diluted with ethyl acetate, washed with dilute hydrochloric acid, an aqueous solution of sodium hydrogencarbonate and brine in order, and dried over anhydrous magnesium sulfate. The solvent was distilled away and the residue obtained was purified by silica gel column chromatography (ethyl acetate:hexane=2:8) to give 13.0 g of 6-cyano-3,4-dihydro-2,2-bis(methoxymethyl)-2H-1-benzopyran-4-one.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 1 hour
  3. customwhile removing the generated water
  4. temperatureAfter cooling
  5. additionthe reaction mixture was diluted with ethyl acetate
  6. washwashed with dilute hydrochloric acid
  7. dry with materialan aqueous solution of sodium hydrogencarbonate and brine in order, and dried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled away
  9. customthe residue obtained
  10. customwas purified by silica gel column chromatography (ethyl acetate:hexane=2:8)

Sources & evidence

ORD record
ord-f72d45b42c804179b1422b549a0c6cc5
Source dataset
uspto-grants-1998_02
Patent number
US05719155

Reaction notes

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